Some synths have built into them a way to modulate some of the enveloped parameters based on MIDI velocity. I'd be almost surprised if expensive packages like that won't do it. Otherwise, one or another of Reaper's modulation/automation options could probably get it working.
In your description, though, it sounds more like the real problem is the first set of notes cutting out too abrubtly. (?) This would be an issue on the Release end of the ADSR, and you might want to mess with that even if you still end up manipulating the Attack Time. Be aware, though, that many synths just can't play the exact same note at the same time. If any one of the 10 notes of the first "chord" is also in the second "chord", then that note will have to abort its Release procedure so that it can retrigger and start the Attack routine. It will cut off short and then fade in.
Again, some synths find ways around that, and I don't know yours specifically. If it turns out that yours is like I described, I think you might have to take that into account in your fingering and arranging. I thought that Philharmonic thing is supposed to have all kinds of things (key switches?) for manipulating articulations. I think if you're just pulling up a preset and banging away like it's a piano, you're wasting a lot of its potential. Read the manual and learn how to play THAT instrument.
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